Benzyl Bromide → Tert-butyl 4-benzyl-3-oxopiperazine-1-carboxylate

HRID 38299

反応式

HRID 38299 の反応式
[H-].[Na+].[C:3]([N:10]1[CH2:15][CH2:14][NH:13][C:12](=[O:16])[CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[O:16]=[C:12]1[N:13]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:15][N:10]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:11]1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

生成物 1

HCID 10891590Tert-butyl 4-benzyl-3-oxopiperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (88 mg, 60% wt.) was added portionwise to a solution of 4-BOC-piperazinone (400 mg) in DMF (10 ml). The reaction mixture was stirred for 1 h, and then benzyl bromide (262 μl) was added dropwise and the mixture stirred at room temp for 16 h. The reaction was quenched with methanol and diluted with water, and then extracted with EtOAC. The organic extracts were concentrated in vacuo and the residue was purified by chromatography (silica, 20% ether/hexane as eluent) to give the sub-title compound (429 mg).

後処理

  1. stirringthe mixture stirred at room temp for 16 h
  2. customThe reaction was quenched with methanol
  3. additiondiluted with water
  4. extractionextracted with EtOAC
  5. concentrationThe organic extracts were concentrated in vacuo
  6. customthe residue was purified by chromatography (silica, 20% ether/hexane as eluent)

出典と根拠

ORDレコード
ord-986826fa224b44c498e4e63b28714e72
出典データセット
uspto-grants-2013_09
特許番号
US08524715B2

関連ノート

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